Manufacture of fast azodyestuffs



Patented June 24, 1930 UNITED STATES aui LE OPOLD LASKA AND ARTHURZITSCHER, OF OFFENBACH-ON-TI HE-MATN, GERMANY,

ASSIGNORS T GENERAL ANILTNE WORKS, INC., OF NEW YORK, N. Y., .A CORPO-RATION OF DELAWARE MANUFACTURE OF IEAST AZODYESTUFFS No Drawing.Application filed August 27, 1928, Serial No. 302,438, and in GermanySeptember 5, 1927.

wherein the aryl residue may contain further substituents. They are whendry reddish to brownish powders, soluble in concentrated sulfuric acidwith a reddish-violet to bluish violet tint. They are especially fast-tolight and therefore outstanding among the preferably fast dyestufis ofthis class. vThe new dyestufl's may be used for manufacturing valuablecolor lakes as well as for producing gist dyeings and'printings on thevegetable In order to further illustrate our invention-the followingexamples are given, the parts being by weight and all temperatures incenti ade degrees; but we wish to be understood that our invention isnot limited to the examples given, nor to the exact conditions statedtherein.

Example 1 19.7 parts of 2.4.5-trichloraniline are di- 40 azotized in theusual manner and the diazosolution is combined with a solution of 30.8parts of-2-hydroxy-3'-naphthoyl 2-amino-1- anisole in a dilute causticsoda solution, containing Turkey red oil and a suflicient amount 4 ofsodium acetate for neutralizing the excess of the mineral acid. Theseparated dyestufi corresponding probably to the formula:

N= Q01 on 1 OO-NH-QOI is filtered off and well washed. It representswhen dry a dark powder and dissolves in concentrated sulfuric acid withareddishviolet tint. It may be advantageously used, in the form of apaste and yields, when mixed with a substratum in the usual manner aclear yellowish red lake of an excellent fastness to light.

In order to produce a dyestufi' of this kind on the fiber one mayproceed as follows:

Ewample 2 Well boiled and dried cotton yarn is impregnated with asolution, containing 6 grs. of 2 hydroxy 3 naphthoyl-5-chloro 2amino-l-anisole, 1-2 cc. of a caustic soda solution of 34 B. and 8 cc.of Turkey red oil per liter, well wrung out and developed with adiazosolution containing 4 grs. of 2.4.5- trichloraniline and beingneutralized with sodium acetate. Then it is rinsed, soaped and dried,

In this manner a-yellowish red dying of an excellent fastness to lightis obtained. The dyestulf thus produced on the fiber correspondsprobably to the formula:

25 1 manufacturing on any substratum especially In the same way ourprocess is carried out when starting from other 2-hydroXy-3-naphthoicacid aryl amides.

The new dyestuffs may also be prepared by the printing process accordingto one of the usual methods.

The following table shows the shades of some dyelngs produced accordingto our 1nvention by combining the diazocompound of 2.4.5-tr1chloran1l1newith:

2-hydroxy-3-naphthoyl-a-naphthylamine 2-hydroxy-8-naphthoyLp-anisidine2-hydroxy 3 naphthoyl-aminohydroquinone-(limethylether2-hydroxy-3-naphthoy1-4-ch1oro-2-anisidine2'-hydroxy-3-naphthoy]-5-ch1or0-2-toluidine Claret red Red yellowish redYellowish red yellowish red bis-[2'-hydroxy-3 naphthoyl]-dianisidineBrown 2-hydroxy-3-naphthoy1-aniline Y c 11 olwtis h scar e Covered redBrownish red Y e110 w i s h 2'-hydroxy-3'-naphthoyl-B-naphthylamine2'-hydr0xy3'-naphthoylp-phenetidine2'-hydroxy-3-naphthoylo-ch1oroaniline scarlet2'-hydroxy-3-naphthoyl-m-chloroani1ine Yellowish red2-hydroxy-3-naphthoyl-p-chloroanlline Yellowish red yellowish red2-hydroxg-3 '-na phthoyl-m-toluidine 6-bromo- -hydroxy-3-naohtboy1 2amino- 5-chloro-hydroquinone-dimethylether We wish it to be understoodthe term manufacturing in the following claims means manufacturing insubstance as well as Copper red on the vegetable fiber.

We claim:

1. As new compounds azodyestuffs corresponding probably to the generalformula:

O O-NH which compounds are when dry reddish to brownish powders, solublein concentrated sulfuric acid with a reddish-violet to bluishviolet'tint, being suitable for the production of valuable color-lakes andyielding, when produced on the vegetable fiber, dyeings and printings ofan excellent fastness to light.

4. Textile material dyed with the dyestuffs claimed in claim 3, saiddyestuffs being pro duced on the vegetable fiber.

5. As a new compound the azodyestuif corresponding probably to theformula:

OO-NH which compound is a dark powder soluble in concentrated sulfuricacid with a reddishviolet tint, being suitable for the production ofValuable color lakes and yielding, when produced on the vegetable fiber,yellowish-red dyeings and printings of an excellent fastness to light.

6. Textile material dyed with the dyestuffs claimed in claim 5, saiddyestuffs being produced on the vegetable fiber.

In testimony whereof, we afiix our signatures.

LEOPOLD LASKA. ARTHUR ZITSCHER.

' Patent Nd. 1,765,681,

' LEOPOLD .LASKA ET L.

c Grented 31111524, 1930 to I Io ie herebycertifiedfihet er r0r eppearsin the printed specification of the above numbered patent requirmgQOIVIGCUOII asvfollows: I I

' Page :1,li1 1es 50130 55, str lke out the formula and msert lnsteaclage 2 ,"'1i}1 e 61 claim 3, after the formula insert whei'e'in the X'smam hydrogen or one X chloMn-e, ajndthat the seidfLetters Patent shouldbe'read with these corrections therein, thatthesame may conform to therecord of the case in o he Patent'Office.

Signed end'e'eled this Zdday ofjSeptember, AQD 1 930.:v I k [SEAL]; v c'M. J; MOORE,

Acting Commissioner of Patents.

